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1-Butyl-3-methylimidazolium hexafluorophosphate

(Redirected from BMIM-PF6)

1-Butyl-3-methylimidazolium hexafluorophosphate, also known as BMIM-PF6, is a viscous, colourless, hydrophobic and non-water-soluble ionic liquid with a melting point[1] of -8 °C. Together with 1-butyl-3-methylimidazolium tetrafluoroborate, BMIM-BF4, it is one of the most widely studied ionic liquids. It is known to very slowly decompose in the presence of water.[2]

1-Butyl-3-methylimidazolium hexafluorophosphate
BMIM cation and PF6 anion
Names
IUPAC name
1-butyl-3-methylimidazol-3-ium hexafluorophosphate
Other names
BMIM-PF6
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.203.179 Edit this at Wikidata
UNII
  • InChI=1S/C8H15N2.F6P/c1-3-4-5-10-7-6-9(2)8-10;1-7(2,3,4,5)6/h6-8H,3-5H2,1-2H3;/q 1;-1 checkY
    Key: IXQYBUDWDLYNMA-UHFFFAOYSA-N checkY
  • InChI=1/C8H15N2.F6P/c1-3-4-5-10-7-6-9(2)8-10;1-7(2,3,4,5)6/h6-8H,3-5H2,1-2H3;/q 1;-1
    Key: IXQYBUDWDLYNMA-UHFFFAOYAH
  • CCCCN1C=C[N ](=C1)C.F[P-](F)(F)(F)(F)F
  • CCCCn1cc[n ](c1)C.F[P-](F)(F)(F)(F)F
Properties
C8H15F6N2P
Molar mass 284.186 g·mol−1
Appearance Light yellow liquid
Density 1.38 g/mL (20 °C)
Melting point −8 °C (18 °F; 265 K)
insoluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Preparation and uses

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BMIM-PF6 is commercially available. It may be obtained in two steps: BMIM-Cl is synthesized by alkylating 1-methylimidazole with 1-chlorobutane. A metathesis reaction with potassium hexafluorophosphate gives the desired compound; the tetrafluoroborate may be prepared by analogously using potassium tetrafluoroborate.[3]

 


BMIM-PF6 has been investigated in electrochemistry where it serves both as solvent and electrolyte.[4] and electrochemical CO2 reduction.[5]

See also

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References

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  1. ^ Mihkel Koel (2008). Ionic Liquids in Chemical Analysis. CRC Press. p. xxvii. ISBN 978-1-4200-4646-5.
  2. ^ R.P. Swatloski; J.D. Holbrey & R.D. Rogers (2003). "Ionic liquids are not always green: hydrolysis of 1-butyl-3-methylimidazolium hexafluorophosphate". Green Chem. 5 (4): 361–363. doi:10.1039/b304400a.361-363&rft.date=2003&rft_id=info:doi/10.1039/b304400a&rft.au=R.P. Swatloski&rft.au=J.D. Holbrey&rft.au=R.D. Rogers&rfr_id=info:sid/en.wikipedia.org:1-Butyl-3-methylimidazolium hexafluorophosphate" class="Z3988">
  3. ^ Dupont J, Consorti C, Suarez P, de Souza R (2004). "Preparation of 1-Butyl-3-methyl imidazolium-based Room Temperature Ionic Liquids". Organic Syntheses; Collected Volumes, vol. 10, p. 184.
  4. ^ Álvaro Pérez-Salado Kamps, Dirk Tuma, Jianzhong Xia, Gerd Maurer (2003), Solubility of CO2 in the Ionic Liquid [bmim] [PF6], vol. 48, pp. 746–749, doi:10.1021/je034023f746-749&rft.date=2003&rft_id=info:doi/10.1021/je034023f&rft.au=Álvaro Pérez-Salado Kamps, Dirk Tuma, Jianzhong Xia, Gerd Maurer&rfr_id=info:sid/en.wikipedia.org:1-Butyl-3-methylimidazolium hexafluorophosphate" class="Z3988">{{citation}}: CS1 maint: multiple names: authors list (link)
  5. ^ Yeonji Oh, Xile Hu (2015), Ionic liquids enhance the electrochemical CO2 reduction catalyzed by MoO2, vol. 51, pp. 13698–13701, doi:10.1039/C5CC05263G13698-13701&rft.date=2015&rft_id=info:doi/10.1039/C5CC05263G&rft.au=Yeonji Oh, Xile Hu&rfr_id=info:sid/en.wikipedia.org:1-Butyl-3-methylimidazolium hexafluorophosphate" class="Z3988">

Further reading

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  • S. Carda-Broch; A. Berthod; D.W. Armstrong (2003). "Solvent properties of the 1-butyl-3-methylimidazolium hexafluorophosphate ionic liquid". Analytical and Bioanalytical Chemistry. 375 (2): 191–199. doi:10.1007/s00216-002-1684-1. PMID 12560962. S2CID 32506513.191-199&rft.date=2003&rft_id=https://api.semanticscholar.org/CorpusID:32506513#id-name=S2CID&rft_id=info:pmid/12560962&rft_id=info:doi/10.1007/s00216-002-1684-1&rft.au=S. Carda-Broch&rft.au=A. Berthod&rft.au=D.W. Armstrong&rfr_id=info:sid/en.wikipedia.org:1-Butyl-3-methylimidazolium hexafluorophosphate" class="Z3988">
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